SYNTHESIS OF C-GLYCOPYRANOSYL COMPOUNDS BY A PALLADIUM-CATALYZED COUPLING REACTION OF 1-TRIBUTYLSTANNYL-D-GLUCALS WITH ORGANIC HALIDES
SYNTHESIS OF C-GLYCOPYRANOSYL COMPOUNDS BY A PALLADIUM-CATALYZED COUPLING REACTION OF 1-TRIBUTYLSTANNYL-D-GLUCALS WITH ORGANIC HALIDES
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DOI：
10.1016/s0008-6215(00)90552-4
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发表时间：
1992-04-10
影响因子：
3.1
通讯作者：
BEAU, JM
中科院分区：
文献类型：
--
作者：
DUBOIS, E;BEAU, JM
以1-苯磺酰基-D-葡糖醛为原料，在钯（0）催化剂存在下，将1-三丁基甲锡酰基-D-葡糖醛与各种有机卤化物有效偶联。 这种温和的反应对于制备1-C-芳基-D-葡糖醛特别有用，并且与未保护的羟基或受阻芳族溴化物相容。 已经表明，所得的1-C-芳基（烷基）-D-葡糖醛适合于烯醇醚基团的进一步合成操作，包括立体选择性氢化、硼氢化-氧化或环氧化。 所形成的所有化合物都是由该试剂对葡萄糖衍生物的α-面的攻击引起的。 该反应扩展到1，3-、1，4-二-和1，3，5-三溴苯，导致相应的对称二-（三）-C-葡糖基苯。 最后，获得了1，3-二溴苯与两种不同的1-锡烷基化葡糖的连续二-C-葡糖基化。
1-Tributylstannyl-D-glucals, prepared from the corresponding 1-phenylsulfonyl-D-glucals, were coupled efficiently to various organic halide in the presence of a palladium(0) catalyst. This mild reaction is specially useful for the preparation of 1-C-aryl-D-glucals and compatible with unprotected hydroxy groups or hindered aromatic bromides. It has been shown that the resulting 1-C-aryl(alkyl)-D-glucals are suited for further synthetic manipulation of the enol ether group, including stereoselective hydrogenation, hydroboration-oxidation, or epoxidation. All compounds formed resulted from the attack of the alpha-face of the glucal derivatives by the reagent. The reaction, extended to 1,3-, 1,4-di-, and 1,3,5-tri-bromobenzenes, leads to the corresponding symmetrical di-(tri)-C-glucosylbenzenes. Finally, a sequential di-C-glucosylation of 1,3-dibromobenzene with two different 1-stannylated glucals was obtained.